tert-butyl 4-<5(S)-<3-(phenylsulfonyl)-5(S)-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4(R)-methylhexyl>-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-2(S)-yl>-3-methyl-2(E)-butenoate

Base Information

• Chemical Name: tert-butyl 4-<5(S)-<3-(phenylsulfonyl)-5(S)-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4(R)-methylhexyl>-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-2(S)-yl>-3-methyl-2(E)-butenoate
• CAS No.: 117438-73-0
• Molecular Formula: C₃₉H₆₄O₉SSi
• Molecular Weight: 737.083
• Mol file: 117438-73-0.mol

Synonyms:

Chemical Property of tert-butyl 4-<5(S)-<3-(phenylsulfonyl)-5(S)-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4(R)-methylhexyl>-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-2(S)-yl>-3-methyl-2(E)-butenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-<5(S)-<3-(phenylsulfonyl)-5(S)-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4(R)-methylhexyl>-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-2(S)-yl>-3-methyl-2(E)-butenoate

There total 12 articles about tert-butyl 4-<5(S)-<3-(phenylsulfonyl)-5(S)-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4(R)-methylhexyl>-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-2(S)-yl>-3-methyl-2(E)-butenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

cycloxexanone dimethyl ketal (933-40-4) → tert-butyl 4-<5(S)-<3-(phenylsulfonyl)-5(S)-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4(R)-methylhexyl>-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-2(S)-yl>-3-methyl-2(E)-butenoate (117438-73-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / p-toluenesulfonic acid / 12 h / Ambient temperature

3: hexane; diethyl ether / Irradiation

4: 1.) n-BuLi, (i-Bu)2AlH, 2.) 4-A molecular sieves, pyridinium chlorochromate / 1.) THF, -78 deg C, 1.5 h, 2.) CH₂Cl₂, RT, 45 min

5: 1.) n-BuLi / 1.) THF, hexane, -65 deg C, 10 min, 2.) -65 deg C, 1 h

With n-butyllithium; 4 A molecular sieve; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; In diethyl ether; hexane;

DOI:10.1021/jo00260a020

Reference yield:

methyl <2(S)-(2-oxopropyl)-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-5(S)-yl>acetate (100703-59-1) → tert-butyl 4-<5(S)-<3-(phenylsulfonyl)-5(S)-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4(R)-methylhexyl>-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-2(S)-yl>-3-methyl-2(E)-butenoate (117438-73-0)

Guidance literature:

Multi-step reaction with 4 steps

2: hexane; diethyl ether / Irradiation

3: 1.) n-BuLi, (i-Bu)2AlH, 2.) 4-A molecular sieves, pyridinium chlorochromate / 1.) THF, -78 deg C, 1.5 h, 2.) CH₂Cl₂, RT, 45 min

4: 1.) n-BuLi / 1.) THF, hexane, -65 deg C, 10 min, 2.) -65 deg C, 1 h

With n-butyllithium; 4 A molecular sieve; diisobutylaluminium hydride; pyridinium chlorochromate; In diethyl ether; hexane;

DOI:10.1021/jo00260a020

Reference yield:

tert-butyl dimethylphosphonoylacetate → tert-butyl 4-<5(S)-<3-(phenylsulfonyl)-5(S)-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4(R)-methylhexyl>-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-2(S)-yl>-3-methyl-2(E)-butenoate (117438-73-0)

Guidance literature:

Multi-step reaction with 4 steps

2: hexane; diethyl ether / Irradiation

3: 1.) n-BuLi, (i-Bu)2AlH, 2.) 4-A molecular sieves, pyridinium chlorochromate / 1.) THF, -78 deg C, 1.5 h, 2.) CH₂Cl₂, RT, 45 min

4: 1.) n-BuLi / 1.) THF, hexane, -65 deg C, 10 min, 2.) -65 deg C, 1 h

With n-butyllithium; 4 A molecular sieve; diisobutylaluminium hydride; pyridinium chlorochromate; In diethyl ether; hexane;

DOI:10.1021/jo00260a020

upstream raw materials:

(2S,3S)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1-(phenylsulfonyl)butane

<2(S)-(2-methyl-3-(tert-butoxycarbonyl)-2(E)-propenyl)-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-5(S)-yl>acetaldehyde

cycloxexanone dimethyl ketal

ethyl (2S,3S)-3-hydroxy-2-methylbutanoate